


7 Tinder Dates

by reillyblack



Category: Supernatural
Genre: Bi Dean, F/M, Fluff, Gay Castiel, I am all about romcom right now, M/M, also Cas is really cranky and kind of a dick, warning for ridiculous levels of romcom
Language: English
Status: Completed
Published: 2015-09-05
Updated: 2015-09-09
Packaged: 2018-04-19 03:43:17
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 7,464
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4731620
Author URL: https://archiveofourown.org/users/reillyblack/pseuds/reillyblack
Summary: <blockquote class="userstuff">
              <p>“My brother’s got cute kids. He and his wife are so--” Dean shrugged. “Maybe I always wanted that, just didn’t think I could find someone who wanted it with me.”</p>
            </blockquote>





	1. Chapter 1

Dean scooped up little John and Mary and ran as fast as he could. A monster screamed behind them.

He ducked around the play set and deposited the two children before he raced back out to face all 3 feet and 5 inches of flailing limbs and high-pitched screaming.

“No, Uncle Dean!” Little Dean squealed. “I had them!”

“Now _I_ have you.” Dean grinned and hoisted his smaller namesake up on his shoulders. “And we form a super monster!”

John and Mary squeaked with delight and scattered from their hiding place. Dean chased them around until he spotted Jessica at the door to the backyard, a plate of fruit in her hand.

“Anyone up for a snack?” she called, a smile on her lips.

Dean set Little Dean down and the three kids ran to their mother, their tiny hands reaching and grabbing unsuccessfully for the bounty on the plate.

“Ah ah!” Jessica frowned. “Sit at the table like you have manners.”

“Then why’d you bring it out to show us?” Mary asked.

“To tempt you away from your uncle.” Jessica winked at Dean.

They followed her inside. Dean stooped to pick an assortment of toys up off the ground. An extra pair of feet and hands started to help him.

“You’re out of your legal bat cave!” Dean grinned at Sam.

“You did a great job keeping them quiet so I could concentrate, by the way,” Sam quipped.

“Oh yeah. Forgot you asked me to do that. Whoops.”

“Yeah, whoops,” Sam grumbled, but he was still smiling.

They carried their armful of toys into the house and deposited them in the toy chest in the living room. The three kids were all eating their fruit quietly, zoned out to the children’s show on the kitchen TV.

“How old are they now?”

“Mary’s 6, John’s 4, and Dean’s 3.” Sam nodded at each of them in turn.

Dean nodded too, still watching them.

“Dean.”

“Yeah? What the hell happened to Sesame Street? Some weird stuff on TV nowadays for kids.” 

“Can I talk to you about something in the other room?”

That got Dean’s attention. He turned to study his brother and found worry in the crease of his forehead.

“Yeah,” Dean followed him quietly into the legal bat cave, filled with law books and things that gave Dean a headache just by looking at them.

Sam sat in a far too cushy chair and Dean did the same. Sam crossed his leg and studied Dean like a client before finally speaking.

“Dean, you need to start looking to settle down.”

Dean recoiled into the chair.

“This is what you wanted to talk to me about all seriously?” 

“You want kids,” Sam said simply. “You want this life, and we both know it.”

Dean frowned at him, but didn’t respond.

“You’re thirty five! And I think you keep doing the hookup thing just because you’re used to it, not because you actually like it anymore.”

Dean opened his mouth to argue but, again, found nothing to say.

“Just do me a favor, as your little brother – go on a date you think could lead to something. Go on several. There’s that app, right? Tinder? I read some research on it, and it’s actually one of the best dating apps out there. Plus, it’s right up your comfort zone, with hookups and whatnot. I bet you already have an account.”

“Impala67,” Dean admitted faintly.

“Great! So ask a few people out on there, take them on a real date, have a real conversation with them about real things, and just try to see if it could go somewhere. If you don’t want to do it for yourself, Dean, do it for me; you’re a great uncle, but I want a shot at being an uncle too.”

 

* * *

 

With a lot of Sam’s pushing, hours worth of Dean fighting him on it and complaining and bemoaning, Sam (or they, whatever) scheduled Dean on seven dates. Dean hadn’t even been on that many dates, real dates, in ten years total.

“I really think that girl with the butterfly tattoo on her shoulder could be a winner. What was her name?”

“Shannon, I think,” Dean muttered, almost shell-shocked from the long afternoon spent fighting his brother over his phone. "Maybe Lucy. I don't remember. We looked at so many, my god..." Dean rubbed his hands over his eyes and stretched in his chair.

“Well, you’ve got the raw looks and charm. It only took me, what, four hours to find seven girls who would go out with you? You realize how many dudes would trade places with you?”

“Sammy, what the hell do you expect me to say to that?” Dean was more testy than he’d been a few hours earlier.

“I expect you to drag your self-esteem off of rock-bottom and give yourself a shot at finding something real, something like what me and Jess have.”

Dean swallowed because that was the crux of his brother’s argument, and one Dean couldn't seem to defend himself against. It hit home. Yeah, he wanted it –- he wanted little rugrats running around, and a beautiful spouse to bake him pies. But yeah, also, Dean didn’t deserve it. Sam went off to law school, and Dean was so fucking proud of him, but he stayed behind to work in his father’s auto shop and lived just down the street from his parents in a modest, one-bedroom house up to his mid thirties. He barely made enough to support himself, let alone a family, whereas Sam had a beautiful home he’d almost completely paid off, and money coming out his ears as a lawyer. The sad truth was that Dean just wasn’t worth much compared to his brother, so why would he even try?

“Dean, please. Just go on a few dates, let loose, and please god don’t treat it like a hookup. You might find something amazing if you give it a shot.”

“Sam, I’ll go on these stupid dates, but no promises that I’m going to marry any of them,” Dean mustered a tiny bit of force from his depleted reserve.

“Ok,” Sam grinned. “That’s fair. No promises.”

 

* * *

 

Date number one was beautiful. She had long dark hair and a physique that made Dean’s mouth water. Her skin was a lovely shade of caramel, her eyes a bright brown. Her name was Carmen and she liked gardening and cooking. Sam picked her for her kind smile.

“Water?” The waiter filled both their glasses without waiting for a response.

“Oh, thank you,” she said. Dean had to admit Sam was right about her smile; she seemed nice.

“So what do you do for a living?” Dean finally found himself asking.

“I’m a nurse. I work at St. Mary’s, nearby here actually.”

“Oh, I’ll have to hurt myself more often,” Dean joked. Her smile faded. “Uh, I’m a mechanic. I lose a fingernail once every two weeks, I swear.”

“Oh, a mechanic. So if I ever got a flat tire, you could help me out?” she grinned.

Dean had a suggestion on the tip of his tongue before Sam’s voice said clearly in his head:  _please god, don’t treat it like a hookup_. He cleared his throat and fished around for something less… hookup-y.

“Uh, I could teach you how to do it yourself, honestly. That’s good for everyone to know.”

“Oh.” Her flirty smile faded for a second time and Dean could practically feel the awkward settle over them both.

Luckily, the food came in just a few more minutes of strained conversation. The waiter gave them each other’s food before switching it to the correct side with a slow apology.

They ate quietly and Dean kicked himself for his lack of anything to say. Usually, he was damn good at this part –- the first part, where they just had to flirt a little and go home at the end of the night to some hot sex. He couldn’t shake the idea that these dates were supposed to be open to more, and that gave him a deep-seated sense of discomfort that left his tongue with none of the witty banter he could usually count on.

“Complimentary dessert for the lovely couple.” The waiter set a plate of delicious pie down between them. He probably felt bad about mixing up their food.

“Hey, thanks, man,” Dean smiled.

“Oh, wow. Cool,” Carmen laughed, forking a piece off the pie.

“Dude, this is my favorite,” Dean gaped. He looked around for the waiter, but the guy was out of sight.

The tone of the date lightened considerably after Dean relaxed to the familiar taste of his favorite pie.

But at the end of the night, when Dean normally would have taken her home with him and done what he’s actually good at, he heard Sam’s voice whispering “marriage material” in his head over and over again and still couldn’t bring himself to turn on the charm.

They somehow didn’t notice the check appear at their table, so Dean never got a chance to thank their kind waiter.

“I had a lovely evening,” Carmen smiled at him outside of the restaurant in the dimming light of the evening. Her lashes were definitely low, an unmistakable invitation written in her coy smile.

“Uh, me too,” Dean didn’t have to lie. It was nice; it just wasn’t, as far as he could trust his gut on these things, marriage level of nice. “I’m kind of busy this week, but I’ll give you a call this weekend.”

Dean promised Sam he wouldn’t make any decisions until the end of the week. Despite that promise, if he trusted his gut, which he almost always did, Carmen wasn’t “the one”.

 

* * *

 

 

Dean’s second date seemed serious, yet soothing. She carried the conversation, which was lucky because Dean was still in the weirded out part of the whole “looking for a soulmate” transition in his dating life.

“So that’s when I realized that my true calling was in the church. I changed my major to religious studies, and that’s what my life's been about ever since 22.”

“Wow. That’s great.” Except that Dean wasn’t religious in the slightest.

“What church do you go to?” Anna tilted her head to the side in soft curiosity.

“Well…”

“Ready to order?”

“Yeah,” Dean, still not even a little bit religious, silently thanked god for the interruption. “I’ll have the fettuccine, and don’t go easy on that sauce now.”

“So, same as last night, then.”

Dean looked over at the somewhat irritable tone. He recognized the waiter.

“Hey! It’s you! I never got to thank you for that complimentary pie. That was the bomb, man.”

“My pleasure,” but it was still somewhat stiff compared to his attitude the night before. He turned to Anna without another word to Dean. “And you?”

“The prosciutto, please.”

Dean definitely couldn’t repeat that, let alone guess at its contents.

“Very good.” And with that he left them to what was sure to be a mood killing moment when Dean revealed his deep lack of any religious upbringing or interest in the such.

They did not receive complimentary pie this time.

 

* * *

 

Dean was a creature of habit, and hell, the food was good, so he found himself on date number three at the same restaurant the next night.

This one’s name was Cassie, and Dean was starting to suspect she might just break his streak of horrible luck. Anna hadn’t immediately dismissed him after his big unreligious confession, but she hadn’t asked him to call her either at the end of the date. Cassie, on the other hand, immediately started up a conversation about a recent sci-fi flick they’d both seen and Dean found it far easier to laugh around her.

“Right? Jack Black is such an idiot. God help me, though, I do love him.”

“There’s something so admirable about a man who can play a ninja panda.”

“Right?” Cassie giggled. “Gosh, everything looks so good. Do you have any recommendations for me?”

“I always get the fettuccini, and that’s awesome. Like, I could eat it forever.”

“Obviously.”

Dean jumped at the familiar voice. That damn waiter was back, and this time he wasn’t even polite about his irritation; it was laid out clear on his face.

Without preamble, the waiter turned to his date and informed her testily, “Ma’am, I feel obligated to tell you that this man has been on two other dates at this very restaurant this week. In all my time working here, I’ve never seen such a thing. I don’t know what’s going on, but I doubt it will work out in your favor.”

At which point Dean’s stomach fell out through his ass and Cassie’s whole face changed as she looked back at him. Her eyebrows climbed to her hairline and her smile dropped quickly.

The waiter left without looking at Dean. Asshole.

“Dean, what’s going on?”

“Well…” Dean was never a good liar. “I’ll just tell you the truth, ok? My brother set me up on a bunch of dates because… I don’t even know why, because he’s an overbearing moose of a brother who cares too much about what I’m doing with my life,” Dean huffed mostly to himself than to her. “Anyway, I like the food here, so I just set them all up here.”

Cassie crossed her arms and leaned back in her chair.

“How many dates?”

Dean blew out long and slow as he nervously pretended to count in his head.

“Hmmm, well, maybe, like, seven?”

“Seven?” Cassie’s eyes bulged. “So, what, we’re all up on the chopping block, and it’s whoever makes the cut? Here I thought you were really interested in my profile.”

“I was! I mean, I, well he actually, only asked out girls I was interested in.”

“Ok. Prove it,” Cassie challenged, raising one eyebrow, “Name three things you liked about my profile.”

“Uh.” They all sort of blended together, honestly. He’d looked at easily thirty girls’ profiles in a four hour span. “I bet you can’t name three of mine!” he eventually landed on, feeling desperate.

“You love cars, especially Chevies, and the woman you admire the most in your life is your mother. You’re hoping to find someone who likes to bake and digs Vonnegut, which, by the way, I do, and you’d know that if you’d cared about my profile,” Cassie shook her head, sighing. “I was so excited for this date. But now… not so much. I think I’m going to take myself out of the competition.”

“Wait, Cassie.” Dean gaped as she gathered her stuff, shot him one last look of disappointment, and left.

Dean sat by himself in the ambience of the restaurant and tried to process what the hell just happened.

“So, just the fettuccine tonight, sir?” That goddamn waiter was back and he sounded all too chipper. He was missing the evil mustache, but he had the villain smirk down.

“What the hell?” Dean hissed. “I thought you were cool. You gave me pie!”

“If you think just because I’m in customer service I have to stand by and watch you screw over some very nice women, think again.” He raised one eyebrow in challenge and added, “And, by the way, we reserve the right to refuse service to--”

“Shit, seriously? Can this night get any worse.” Dean sank his eyes into his palms and deflated onto the table. “I blame Sam for this.”

“This appears to be no one’s fault but your own.” Oh great, the waiter was possibly even more pissed off. “Maybe you should take a little responsibility for treating people with a lack of respect.”

“Dude, they were first dates, ok? And I wasn’t going to actually _date_ all of them and… three-time them, or whatever you were thinking. These were meet and greets with no commitment. I’ve been on a ten year vacation from actually dating and I was trying again and I’m supposed to be…” No, no Dean was not going to tell this random asshole that his brother put him on a haphazard, poorly planned mission to find his soulmate.

The waiter wasn’t exactly glaring at him anymore; more like cooly judging him, which wasn’t much better.

“How many ‘meet and greets’ do you have planned while sitting in my section?” he demanded.

“Believe me, I’ll avoid your section like the plague after this, but could you not ban me from my favorite fucking restaurant? I’d really appreciate it.”

The guy’s frown deepened, but Dean could see the pity winning out over irritation, finally.

“I’ll consider it.”

“Great. So, why don’t you wander off and ruin someone else’s night while you’re thinking it over? I just need a few moments to scrape my dignity off the floor and I’ll be out of your section.”

The guy paused, but then turned on his heel and scurried off out of sight. Dean sank his eyes back into his palms and let himself sag.

She’d been so cool, too. He’d really liked Cassie (what little he’d seen of her). Now he was that asshole she’d never talk to again, and possibly an asshole about to be thrown from his favorite restaurant, especially after cussing out the waiter.

Dean picked at his nail beds and willed himself to get up out of the seat and just leave; he should go home and run a hot bath and soak in his depression at a week filled with a weird level of anxiety and awkwardness and exhaustion. He was trying too hard for something he didn’t even want to want.

He was still silently arguing with himself when a plate of fettuccine slid under his nose.

“Sorry I wrecked your date,” the waiter still sounded pissed off, but when Dean looked at him he seemed more pitying than annoyed. “Eat your food and stop moping.”

“Now I’m a man eating alone in a restaurant. I'm allowed to mope about that,” Dean complained almost without thinking.

The guy sighed softly, his nostrils flaring and his eyebrows tweaking together briefly. Then he left Dean to his bad mood once more.

Dean got about halfway through the fettuccine before the waiter appeared again, carrying a slice of pie. This time he slid into the booth where Cassie had been and silently placed the pie between them. He had another plate of food that Dean definitely didn’t order and didn’t want to eat.

“I’m on my break,” he informed Dean stiffly.

“Ok.” Dean blinked at him.

“I’ll… I chased your date away when I didn’t know the situation and now you look like I ran over your puppy or something. I’ll keep you company while you eat,” he tried again, some of the hostility gone from his voice. Apparently the extra plate of food was for him because he started in on it.

Silence settled over them, which was perfectly fine with Dean as he was still pretty moody about the whole situation despite the waiter’s change of attitude.

“Why haven’t you dated in ten years?”

Dean looked up, startled once more. The guy had bright blue, piercing eyes that unnerved Dean more than a little bit now that they were totally focused on him. Dean cleared his throat.

“I don’t know.”

“You must have a good reason for that. You just decided not to date during your twenties? Most people do the exact opposite.”

“They, what, super date?”

“Yes, they date as much as possible,” the guy seemed to miss Dean’s dark amusement. He was staring at Dean again with those intense eyes.

“I don’t know. Dating’s not for everyone. I just didn’t feel up to it.”

“And you’re up to it now?” the waiter took another bite of his food. “Why?”

“Shit, is this the inquisition?” Dean grumbled.

“I’m letting you eat your food, aren’t I?” the waiter squinted at him dangerously. “Was that a mistake?”

Damn, it was good fettuccine.

“My brother’s got cute kids. He and his wife are so--” Dean shrugged. “Maybe I always wanted that, just didn’t think I could find someone who wanted it with me.”

Shit. That was too honest. He’d gone straight from no answer to too much answer in five seconds. Shit shit shit.

“You,” the guy swallowed his food, staring at Dean, “you liked her more than the others, didn’t you?”

“Doesn’t matter.” Dean shrugged again. “She’s gone now.”

“Sorry,” the waiter said softly.

“No, I can see how I must’ve looked like an asshole. I probably should have picked a different restaurant, but I just love this place.”

“You did look like an asshole,” the waiter agreed with a dry smile. “I’m not going to beat myself up too much.”  
Dean snorted and rolled his eyes. _Who’s the asshole, huh?_

“I’m Castiel,” the waiter said into his food.

“Dean,” Dean grunted in return.

 

* * *

 

 

Somehow, Castiel managed to pry the intimate details of Dean’s dating history out of Dean’s unwilling mouth. Dean didn’t know how it happened. The guy had… had these crazy intense eyes that, like, hypnotized Dean and convinced him to overshare.

“You’re an idiot.” Castiel leaned back in his chair and shook his head. “Lisa was in love with you, and you blew it.”  
Ok. Uncool.

“Yeah, so in love with me that she tied the knot with Ben’s bio dad, like, six months after we broke up.”

“Irrelevant.” Castiel waved it off. “That could have been you if you hadn’t bailed.”

“Oh, fuck off,” Dean snarled. Castiel only leaned in farther, a bright spark of determination in his eyes.

“She was the one who invited you to live with her. She let you take Ben out wherever, and didn’t even tell you to call and check in? That’s a heck of a lot of trust for boyfriend. And then she asked you to come back after you left.”

“I cannot believe you’re lecturing me on dating when you can’t even identify sarcasm,” Dean scoffed.

Castiel turned bright red. Dean smirked. Turning the tables seemed to be working, so Dean went for it.

“What’s your deal, anyway? You got a girlfriend or a wife?”

“No,” Castiel sounded suspicious.

“Well, you _must_ be an expert.”

“I’m not that interested in women.” Castiel’s mouth quirked up into a quick, ironic smile.

Dean fish gaped for a second, caught off guard.

“Oh.”

“Yeah.”

“So. Ok.” Dean gathered himself up.”Then, you got a boyfriend or a… husband?”

“...No,” Castiel answered more sullenly.

“Hah! I win.” Dean smiled triumphantly.

Castiel quirked another half-smile. “I think we’re both losers here.”

“What? No. We’re just… biding our time. Late bloomers. Or something.”

“Or you’re struggling with dangerously low self esteem, and I have no ability to maintain intimacy,” Castiel said quietly.

Well shit, now he’d bummed the guy out.

“That can’t be true. We’re maintaining intimacy right now. Ok, that came out wrong.”

“Dean, I am an expert in telling you how you push people away for a good reason.” Castiel’s frown deepened to something similar to what Dean’s face must have looked like a half an hour ago when Cassie left.

“Dude, come on. Only one of us needs to be depressed at this table.”

“No, you’re right. I’m just as much of a pathetic mess as you,” Castiel moped suddenly.

“Hey, now.” Dean frowned, irked.

“I’ve been in four long-term relationships, and I sabotaged all of them, just like you sabotaged your relationship with Lisa.”

“Hey.” Dean blinked at the sudden change in positions. Castiel looked genuinely upset. “Dude, you’re… you’re a great guy. You brought me two complimentary pies, for christ’s sake.”

“Dean.” Cas shook his head. “I just broke off a three year relationship because I… I didn’t want to share an apartment with him. I’m very particular about my stuff.”

“Seriously?” Dean squinted.

“Yes,” Castiel moped. “There was absolutely nothing wrong with him. He was a perfectly nice person.”

“Sure.”

“What?” Castiel must have caught his disbelief.

“Well, damn Cas, ‘perfectly nice’ doesn’t sound like you were exactly soul mates either.”

“There was nothing objectively wrong with him that a decent person couldn’t overlook,” Cas sniffed.

“See? That’s not very… look, that sounds like the dryest relationship ever, no offense man.”

“What? What about it?” Cas took offense.

“Seriously? Dude, you’ve gotta have some _heat._ You can’t just date someone because you don’t mind them. You’ve gotta _want_ them. You’ve gotta, like, clash a little bit.”

“Neither of us is really qualified to be giving the other advice,” Cas sniffed, but he was eyeing Dean with interest.

“Maybe you just didn’t like the guy enough to make a big compromise like moving in together.”

“Hm.”

“Oh, I’m right! I am.” Dean grinned.

“I didn’t say that.”

“Didn’t have to. I can see it in those judgey eyes.”

“...Hm. Weak evidence.”

“You are something else,” Dean sighed.

Castiel grinned at him briefly before he sighed too.

“I’ve got to get back to work. My break was over… two minutes ago.” Castiel glanced at what Dean assumed was a clock behind his head.

“Oh no. Scandalous.”

“I’m never late if I can help it.”

“I see that.”

“Dean, you can bring the rest of your dates to my section. You should; I give my friends free pie. You have my word that I won’t chase them off again.” And then he was gone, walking briskly to the door to the kitchen. 

 


	2. Chapter 2

Dean did bring his next date to Cas’s section.

“My main hobbies are knitting and martial arts."

"Sweet combination. I can respect that, Layla."

"What are some of your hobbies, Dean?"

"I'm a big fan of old cars, classic rock, and, well, science fiction flicks." They both chuckled at Dean's nervous admission of nerdiness. "Hey, have I met you before?"

"I’m in real estate, so you might have seen my face on a billboard or something, smiling really big. They make us smile like that, honestly, and I’m always a little embarrassed about it.” 

“I think that's it. You have a beautiful smile, if that helps,” Dean offered. “Can I see your card? It can’t be that bad.”

They were bickering over the level of goofiness on her card when Cas swooped in. Dean was relieved to see his smile this time rather than a judgmental stare.

“Good evening.”

“This is my friend, Cas,” Dean introduced him to Layla.

“Well, friend might be stretching it,” Cas frowned. Then he winked and broke back into a smile. “I promise to take good care of you tonight. Have you had a chance to look over the menu?”

“Not yet. Do you have any recommendations?” Layla asked.

“Absolutely.” Cas rattled off more italian names than Dean could keep track of, though the descriptions made his mouth water. “I’d also recommend the Cabernet Sauvignon, it goes well with almost anything on our menu. I can give you a taste if you’d like?”  

“Thank you, yes please.”

And then Cas winked at Dean again as he was turning to leave.

“Thanks Cas.” Dean almost rolled his eyes at all the winking. What a dork.

“How do you two know each other?” Layla wanted to know.

“Uh,” Dean scrambled while trying not to look like he was scrambling before settling on, “I go here a lot.”

“Oh, so maybe I should have asked _you_ for a recommendation.”

“Unwise. He’s quite unadventurous. He always goes for the fettuccine.” Cas was back, wine bottle and glasses in hand. Dean cleared his throat meaningfully, but Cas didn’t take the hint.

“I know what I like.” Dean tried to make that sound romantic to repair Cas’s unflattering description of him. He heard something like a snort from Cas and the dude almost spilled the wine he was pouring.

Rude.

Layla, on the other hand, seemed to buy what Dean was selling. She leaned in more, smiling gently.

“I like that in a man.”

Another muffled snort from Cas. Dean shot him a glare. How Layla hadn’t noticed Cas’s judge-y reactions was beyond Dean, but she was still looking at him dreamily. Ha. Dean had game, no matter what Cas thought of it.

Dean reached out and threaded his fingers through hers across the table, and then Layla’s smile went sort of shy as she returned the gesture, stroking her fingers along his.

Thankfully, Cas left without another word (or sound).

The wine was good, but neither of them wanted another glass beyond what Cas offered them. Layla picked something from Cas’s recommendations and it turned out to be good enough to coax suspiciously sex-like sounds from her. It was Dean’s turn to wink at Cas from across the restaurant, which for some reason visibly embarrassed the other guy.

Ed Sheeran started up in the ambient music and Dean actually managed to slide their conversation into a romantic enough territory for some across-the-table kisses.

Cas sported a comically disgusted face from two tables over as Dean leaned back from one such kiss, prompting Dean to roll his eyes in return.

The complimentary pie made up for it, as did leaving their wine “tasting” out of the bill.

Dean left him a generous tip as a thanks. It was the best date of the week, though oddly Dean couldn’t decide if he liked Layla any more than the other girls he’d met.

 

* * *

 

Date number five didn’t go nearly as smoothly.

“I’m Michael.” The guy smiled pleasantly at him from across the table, and Dean could almost say for sure that he was more attractive than Dean himself, which was arguably Dean’s best selling point. Three seconds into the date and Dean already felt inadequate.

“Dean.” Dean leaned over to shake the guy’s hand. Michael’s hand lingered for a moment too long.

“This is a great restaurant, I like your taste in food already,” Michael looked around approvingly. “I came here with my ex once. The fettuccine’s good.”

“It is good,” Dean grinned. Ok, he liked this guy a little more. “I agree.”

“You’re even more handsome than your picture.”

Dean flushed at that. Dudes always seemed to be more up-front about Dean’s looks.

“Thanks, man. You’re… uh, something else yourself.”

Michael smiled like he knew perfectly well.

“I work in management,” Michael moved on. “I’m upper level at a company called Sandover. Very competitive business, so I work a lot and don’t have much time to meet people. That’s why I started using tinder. What do you do?”

“Uh, I’m a mechanic at Bobby’s.” Dean shrank into his seat a little bit. MIchael’s smile seemed to widen.

“Dean, don’t worry about the difference in our jobs. I’d love to date someone I can spoil.”

And that seemed pretty demeaning. And also a little tempting. But mostly demeaning.

“Ok…” Dean replied, unsure how else to respond. He pretended to study his menu carefully instead of thinking of something else to say.

Cas had to clear his throat before Dean noticed him, and even then Cas was too busy staring at Michael to acknowledge… Dean acknowledging him. Michael didn’t seem too upset about it, the jerk probably had people staring at him wherever he went. Cas was more… glaring than gaping over his obvious good looks, though.

“Cas, I’m over here. Thanks.”

“Oh, you two know each other?” Michael noted, still looking over his menu.

“I thought we did.” Cas finally turned his eyes on Dean, and dang, they were practically on fire. “What can I start you two off with?” he grit out. Dean flashed back to date number three, to how Cas looked right before he scared Cassie off. Though, if Michael’s arrogance was anything to go by, Cas might actually be doing Dean a favor in repeating that previous offense.

“I’ll get my usual, thanks.”

“Your _usual_?” That was definitely a venomous tone.

“The chicken parmesan looks good. I’ll buy, Dean. Get whatever you’d like,” Michael smiled at him again in that almost predatory way. Dean squirmed in his seat, but he wasn’t about to fight the guy over the bill just to make a point.

“Yeah, my usual is great,” Dean sighed.

“Great.” Cas snapped before turning on his heel.

It was going to be a long night.

 

 

* * *

 

 

Michael turned out to be not that bad, just a bit of a control freak. He was big on asserting his prowess in general, but he did ask Dean thoughtful questions and seemed genuinely interested in his responses, which earned him back some points.

Cas, on the other hand, was a bloody nightmare. He was surly. He refused to meet either Dean’s or Michael’s eyes when he served them. He didn’t even check to see if they were enjoying their dinner -- in fact, he didn’t check to see if they wanted dessert, and apparently forgot about the pie. He just plopped the bill down without stopping on his way to serve another table.

“Your friend looks like he’s having a bad night.”

“Yeah, no kidding.” Dean frowned, watching Cas interact with other customers. Cas seemed to have little problem at least faking nice with people at other tables. What the actual fuck?

“Well, since he’s your friend I’ll still leave him a good tip.” Michael signed the receipt, barely glancing at it. “I’d like to take you somewhere else for dessert, if you don’t mind, Dean?”

“Sure.” Dean was too distracted  trying to figure out what the hell was wrong with Cas to think much about it.

It wasn’t until they were standing by Dean's Impala and Michael gave him his address to follow him back to his apartment that Dean realized they were breaking his no houses (and thus no hooking up) rule for the week.

“I thought we were getting dessert?” Dean said instead of what he was thinking, staring at the card with Michael’s address and trying to find a polite way out of the situation.

“I made a delicious rum cake yesterday,” Michael explained.

_Cake._

“Actually, uh, I have to get up early tomorrow morning, so raincheck?”

“Really, Dean?” Suddenly Michael was crowding him up against the Impala, and Dean felt his ass hit the window before he even realized he’d moved. “You have to get up early? That’s your excuse? I thought we were having a nice time.”

Michael’s breath felt hot against his neck and then it was warm and wet. Dean groaned and sank his head back against the conflicting feelings of panic and arousal.

“We were.” Dean somehow managed to pull himself together and push Michael back a few steps. “I’ll call you this weekend.” _But not with good news, dick._

Michael huffed for a moment and looked like he might argue. Once he collected himself, he seemed satisfied enough to nod his agreement. Michael sauntered off and left Dean to an uncomfortable erection and erratic breathing against the side of his car.

Dean slid into the driver’s side and leaned his forehead against the steering wheel. He took a few deep breaths to steady himself before a knock came at his window.

He was expecting Michael, but was relieved (and confused) to see Cas instead. Well, relieved until he remembered his shitty attitude all night.

“Your wallet.” Cas handed the leather wallet through the window as Dean cranked it down. “You left it at the table.” Ah yes, he'd attempted to pay before Michael batted him off. 

“Thanks. Hey, little thing -- what the hell’s up your ass tonight?”

Cas’s blank expression settled into a scowl.

“You…” he struggled for words for a moment. “I’ll see you tomorrow?”

“I don’t know, man. I might request a different section if I can expect that kind of five star treatment.”

“You’re interested in men,” Cas breathed quickly. He was unreasonably pissed about that fact.

“So? So are you!” Dean returned, completely confused. He obviously wasn’t being homophobic since… well. What was his problem, then? Did he just have a problem with bi guys? Wouldn’t be the first gay guy Dean knew to act like that.

“That’s not--” Cas bit his own words off, working his jaw and glaring at Dean through the sliver of the window. “You didn’t tell me!”

“I’ve known you all of a week! Not even that, actually. What, was I supposed to give you a bi card when I met you or something?”

“That would have been nice, yes.” Ugh, Cas and sarcasm. Just the worst.

“Seriously, Cas? Seriously?”

“You could have at least mentioned it in all the time we were discussing your dating history,” Cas growled.

“Didn’t come up.” Dean shrugged. “I don’t know what to tell you.”

Cas scowled and then he was gone, just like he always seemed to be able to do, walking quickly back up the road to the restaurant.

“Asshole,” Dean breathed to himself as he watched Cas’s retreating figure.


	3. Chapter 3

**Notes for the Chapter:**

> Prefacing this chapter with a whole-hearted apology for being an incredibly cheesy person with a lame sense of humor. 
> 
> (Also I may have marked this as Explicit when it's more like Mature, but I also marked it as complete when it was a wip, so... I'll try to get better at that)

It wasn’t until Dean was sitting in the break room at lunch the next day, eating his sandwich and numbly thumbing through his phone, that he decided to check his tinder notifications. He had three new messages. Two were from women he didn’t know, asking if he wanted to meet up.

Dean almost dropped his sandwich at the third one.

_It’s Castiel._

Dean set his sandwich down just in case he actually did drop it.

_I know you have a very busy schedule of dating douchebags, but I can offer you nearly unlimited free pie. Also, I won’t molest you in the parking lot._

Dean stared at the message until his brain rebooted and his fingers finally clicked into action.

**sometimes I like a little parking lot action**

Just as Dean started to panic that Cas wouldn’t understand that he meant action _with Cas_ in the parking lot, Cas messaged back.

_You are cheesier than the food you eat_

Dean grinned at his phone. Then, just to be sure,

**You know I meant with you, right?**

_I was hoping_

**He was kind of a dick**

_He thinks a lot of himself._

**Understatement**

Dean smiled.

 **You were kind of a dick too**.

_You try waiting on your crush through five dates before you realize you’ve got a shot. See how you feel._

Dean paused, biting the inside of his cheek and listening to the hammering of his heart in his ears.

**My last date canceled on me tonight. Guess I could pencil you in.**

_We are not going to where I work for a date._

**My place?**

This time the response took longer than usual. Dean jiggled his leg.

_I’ll bring pie._

 

* * *

 

 

Cas showed up in a button-down dark blue shirt and khakis, like he dressed for a job interview. Dean, in his jeans and t-shirt, looked him up and down with a critical eye.

“Nice.” Dean grinned.

“I wasn’t sure...” Cas stuttered before handing Dean a whole pie. “I have a feeling you can finish this if you try your best.”

“Damn straight I can,” Dean said, pleased. “Ooh, blueberry. Sweet. I made meat so I hope you’re not a vegetarian or something?”

“I like meat.”

They stared at each other as that statement settled over them. Cas turned a deeper shade of red but didn’t look away.

“Guess I already knew that,” Dean joked eventually. At least they were both in the same state of mind; Dean broke his no houses rule for Cas and he spent more time on every one of his dates watching the waiter’s ass than he spent thinking of new conversation topics for his actual dates. That allowed for a little rule breaking.  

Cas was suddenly kissing him. It was soft and hesitant, despite how eagerly Cas stepped into Dean’s space. Dean moaned at the taste of Cas in his mouth, closed his eyes, and… it was over, Cas leaning back to check his expression.

“Technically, this is our second date. I stole a date from you already this week. We just didn’t know we were on a date at the time.” Cas licked his lips, his eyes flicking between Dean’s. Dean’s hand rested gently on Cas’s hip and Cas was warm under his palm. “You… you like this kind of thing, right?”

Dean somehow knew Cas was talking about the way Michael kissed him in the parking lot, though Dean couldn’t say where that telepathic knowledge came from. Assertive? Hell yeah. Arrogant? Nah.

“Do you?” Dean didn’t want him doing anything just because he thought Dean would like it, but Dean had that same uncomfortable erection starting in his pants so there was no denying how he felt about Cas’s bold move.

Cas answered that by staring at his lips and leaning in again, more confident in how he kissed Dean the second time.

They untangled long enough to get inside the house and to the kitchen. Dean had every intention of serving Cas dinner. Inexplicably, though, Dean found himself pressed up against Cas and the counter, and suddenly he was sitting on the counter, and then Cas was sinking to his knees and unzipping Dean’s jeans.

“I should… put this stuff away…” Dean panted, watching Cas mouth at his boxers.

“You want me to stop?” Cas asked earnestly, his deep blue eyes peering up at Dean at an impossibly hot angle.

“Not for anything,” Dean groaned.

“You said I needed heat.”

“Yeah.”

Cas swallowed him down in one stroke and Dean thought he might see spots.

“I needed to clash with someone.”

“We got that down,” Dean closed his eyes, trying to focus through the wet slide of Cas’s lips on his cock. What a bastard for trying to keep up a conversation when he was doing this to Dean. Thankfully, Cas never got around to any sort of point, which was lucky since Dean couldn’t form words more complex than “oh god”, “Cas”, and “yes”.

Dean felt completely boneless when Cas wiped his mouth off on the back of his hand and stood to kiss Dean.

“I really like meat, actually.”

Dean almost whimpered.

“You’re going to love dinner, then,” Dean said weakly. “If we can ever get to it.”

Cas cracked a grin before needlessly helping him off the counter. Ok, not needlessly; maybe Dean’s knees were a little weak and he appreciated the extra hand.

“I can’t believe you sucked me off in my kitchen on our first date.”

“Second date,” Cas corrected. “So it’s cool.”

Dean laughed.

“It would be cool at any point, as far as I’m concerned.”

“Noted.” Cas straightened his clothes primly as though he hadn’t just been licking Dean’s groin on Dean’s kitchen floor.

Sitting down to eat after that seemed surreal to Dean, but somehow they managed it. Cas’s reassurance that this wasn’t a first date soothed Dean’s nerves somewhat, and he found himself easily bickering and laughing with Cas like they weren’t two near-strangers.

Cas’s favorite color was blue, like his too formal shirt. He liked to study biology in his free time and watch documentaries on animal planet. He had a million brothers and sisters, all named after angels. He was a police officer for ten years before he got fed up with the system and decided to wait tables while he figured out what else he could do. He volunteered with a wildlife preserve every other Sunday.

After Cas helped him with the dishes, they started up a pre-agreed upon movie (Mad Max) and made out on the couch instead of watching it.

Dean had his head on Cas’s chest, eyes closed, when Cas said, “I’m afraid of intimacy. You’re insecure. How’re we going to make this work?”

Dean thought for a moment.

“Prayer?”

Cas snorted. Someone shot at something and screamed on the screen. Dean let his eyes go unfocused on the colors of the tv, in a sort of happiness haze that felt more like dream than reality. For someone who'd supposedly wrecked his last real relationship out of insecurity, Dean felt pretty damn secure. And Cas was doing a great job at the intimacy thing already on the first, no second, date. 

“As long as we both know we’re fucked up, maybe we can work it out,” he mumbled.

“You’re not fucked up.” Cas kissed the top of his head and Dean closed his eyes, falling slowly into sleep.

“I really want this to work.”

Dean wasn’t sure who said it. He felt it, though, in his bones: something right. He hadn’t asked Cas how many kids he wanted, or whether he wanted to live in Lawrence his whole life like Dean did, but he didn’t feel like he needed to. Besides, Sam would undoubtedly use his lawyering skills to make a spreadsheet checklist of goals, dreams and deal-breakers for Dean to go through and fill out with Cas, but hopefully he'd wait until they were a few months along. 

Dean never called anyone back like he promised he would.

**Notes for the Chapter:**

> I had another chapter that I scrapped, but I'm always game for epilogues so maybe I'll try it out for a spin as an epilogue. We'll see.


End file.
